Purpose: To investigate individual and contextual antecedents of learning, transfer of learning, training generalization and training maintenance in a work context. Design/methodology/approach: The hypotheses were tested using hierarchical regression analysis on data obtained from 119 employees who attended training programs. Findings: The data supported the relationship between continuous-learning culture and supervisor support and training motivation. Although training motivation was directly related only to training maintenance, it interacted with performance goal orientation in affecting training transfer and generalization. Practical implications: Practitioners interested in designing interventions directed at increasing similar training outcomes can use various approaches aimed at assessing and monitoring factors such as continuous-learning culture, supervisor support and training motivation. More importantly, based on the current results, practitioners can manage selectively the performance goal orientation of their trainees, given its differential relationship with training outcomes. Originality/value: The findings are valuable for researchers and practitioners. From a theoretical perspective, the study offers a better-specified model of training effectiveness by including both contextual and individual factors important for improving training effectiveness. Practitioners can use these ideas to design corresponding training and training transfer interventions. (Contains 3 figures and 3 tables.)